Google’s Chrome OS includes a shell environment known as Chrome Shell, or “crosh” for short. Crosh includes several terminal commands that can be used on all Chromebooks, even if developer mode isn’t enabled.

First thing I do is run tmux on the machine I ssh to. That will keep the session alive as it updates the time once a minute. You can also do split screen to multiple hosts from the one you run tmux on. (Screen would probably work too).